The Journal of Organic Chemistry

Preparation and reactions of 2, 2-dimethyl-4-cyclopentene-1, 3-dione

WC Agosta, AB Smith III

Index: Agosta,W.C.; Smith,A.B. Journal of Organic Chemistry, 1970 , vol. 35, # 11 p. 3856 - 3860

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Citation Number: 37

Abstract

Treatment of 3 with N-bromosuccinimide yields 1. Simple addition-elimination reactions of 1 and the related ketone 6 give 9, 10, 11, and 14. Enedione 1 is a sluggish dienophile relative to the parent compound 18, but it behaves as a normal dipolarophile. The mechanistic implications of these observations are noted and the structure and stereochemistry of adducts of 1 with cyclopentadiene, three anthracenes, two aairidines (24 and 25), and ...